Hydrochloric Acid → 1-(2-amino-3,4,5-trimethoxyphenyl)-2-(N-methylsulphamoyl)ethanone

Participants

Reaction Steps

To a stirred solution of N-methylmethanesulphonamide (13.6 g) in dry tetrahydrofuran (160 ml) at -70° to -60° was added a solution of n-butyl lithium in hexane (2.5M; 100 ml) under argon. The mixture was stirred at -78° for 1 hour and a solution of methyl 2-amino-3,4,5-trimethoxybenzoate (10 g) in dry tetrahydrofuran (50 ml) was added at -70° to -60°. The mixture was stirred for 2 hours, during which time the temperature rose to 10°. The mixture was poured on to ice (500 g), acidified to pH 1 with 5N HCl, and then neutralised to pH 7 with saturated aqueous sodium bicarbonate. The solid product was extracted into dichloromethane (3×500 ml). The extract was dried and evaporated to give a residue. This residue was triturated with ether to give a solid which was collected, dried and crystallised from ethyl acetate to give the novel compound 1-(2-amino-3,4,5-trimethoxyphenyl)-2-(N-methylsulphamoyl)ethanone, m.p. 125°-127°.

Provenance & Evidence